5495-84-1

Basic information

• Product Name: 2-Isopropylthioxanthone
• Synonyms: SPEEDCURE ITX;QUANTACURE ITX;SPEEDCURE 2-ITX;2-Isopropylthioxanthon;Photocure-Itx;2-Isopropylthioxanthen-9-one;9H-Thioxanthen-9-one, 2-(1-methylethyl)-;2-isopropylthioxantone
• CAS NO: 5495-84-1
• Molecular Formula: C₁₆H₁₄OS
• Molecular Weight: 254.35
• EINECS: 226-827-9
• Product Categories: Functional Materials;Photopolymerization Initiators;Aromatics;Sulfur & Selenium Compounds
• Mol File: 5495-84-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 76 °C
• Boiling Point: 398.9 °C at 760 mmHg
• Flash Point: 210 °C
• Appearance: /
• Density: 1.199 g/cm³
• Vapor Pressure: 1.43E-06mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: 340μg/L at 20℃
• CAS DataBase Reference: 2-Isopropylthioxanthone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Isopropylthioxanthone(5495-84-1)
• EPA Substance Registry System: 2-Isopropylthioxanthone(5495-84-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 20/21-58
• WGK Germany: 3
• Hazardous Substances Data: 5495-84-1(Hazardous Substances Data)

Usage

Chemical Properties

2-Isopropylthioxanthone is light yellow solid with general solubility, effective at low concentration. The absorption wavelength is 250~400nm.

Uses

2-Isopropylthioxanthone is a thioxanthone derivative useful as photoinitiators.

Application

2-Isopropylthioxanthone has been used as an analytical standard for the determination of the analyte in packaged food materials using liquid chromatography-tandem mass spectrometry (LC–MS/MS). It may be used as an analytical standard for the determination of the analyte in milk, fruit drinks and packaged beverages by high performance liquid chromatography (HPLC) coupled to MS/MS and micellar electrokinetic chromatography techniques (MEKC).

General Description

2-Isopropylthioxanthone is a compound, which can play the role of a sulfur type photoinitiator in printing industries and UV-cured inks for food packaging materials.

InChI:InChI=1/C16H14OS/c1-10(2)11-7-8-15-13(9-11)16(17)12-5-3-4-6-14(12)18-15/h3-10H,1-2H3

Synthetic route

Isopropylbenzene (98-82-8) + 2,2'-dithiobenzoic acid (119-80-2) → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With sulfuric acid at 20℃; for 0.5h;	99%
With methanesulfonic acid; zinc In chlorobenzene at 115℃;	89.5%

2-isopropyl thioxanthene → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 12h; Irradiation;	98%
With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 12h; Sealed tube; Irradiation;	98%
With potassium hexafluorophosphate; iron(III) nitrate monohydrate; oxygen In acetonitrile at 80℃; for 2h; Reagent/catalyst; Temperature; Concentration;	96%
In 1,2-dichloro-ethane at 20℃; for 2h; UV-irradiation;	75%
With air In 1,2-dichloro-ethane at 20℃; for 2h; UV-irradiation;	75%

2-(4-isopropylphenylthio)benzoic acid (5495-75-0) → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With sulfuric acid In cyclohexane Solvent; Temperature; Reflux;	91%

Isopropylbenzene (98-82-8) + 2-chlorosulfenylbenzoyl chloride (3950-02-5) → 4-isopropylthioxanthone + 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 0.5h; Product distribution / selectivity; Friedel Crafts Acylation;	A 9.8% B 88.2%
aluminum (III) chloride In 1,2-dichloro-ethane at -10 - 25℃; for 1 - 1.25h; Product distribution / selectivity; Friedel Crafts Acylation;	A 11.2% B 76%

Isopropylbenzene (98-82-8) + 2,2'-dithiobenzoic acid (119-80-2) + Benzotrichlorid (98-07-7) → 4-isopropylthioxanthone + 2-isopropyl-9H-thioxanthen-9-one (5495-84-1) + 3-isopropylthioxanthone

Conditions	Yield
Stage #1: 2,2'-dithiobenzoic acid; Benzotrichlorid With iron(III) chloride In chlorobenzene at 100℃; for 1h; Inert atmosphere; Stage #2: Isopropylbenzene With aluminum (III) chloride In trans-1,2-dichloroethylene at 20℃; for 1h; Inert atmosphere; Overall yield = 32.8 g;

2-chloro-2'-ethoxy-5'-isopropylbenzophenone → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With copper; sodium carbonate; sulfur In 1,2-dichloro-ethane Solvent; Reagent/catalyst; Reflux;	20.8 g

2-chloro-2'-methoxy-5'-isopropylbenzophenone → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With copper; sulfur; sodium hydroxide In 1,2-dichloro-ethane Solvent; Reagent/catalyst; Reflux;	20 g

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 2-isopropyl-9H-thioxanthen-9-one 10,10-dioxide (210295-96-8)

Conditions	Yield
With Oxone In methanol; water Heating / reflux;	82%

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 2-isopropylthioxanthone sulphoxide (482662-60-2)

Conditions	Yield
With cerium(IV)diammonium nitrate In water; acetonitrile at 20℃; for 2.5h;	52.3%
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃; for 2.5h;	52.3%
With dihydrogen peroxide; trifluoroacetic acid In water at 0 - 23℃; for 12.25h;

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C29H26OS

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol 2.1: perchloric acid / toluene; water 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -84 °C / Sealed tube; Inert atmosphere 3.2: 1 h / 20 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C30H28OS

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanol 2: perchloric acid / toluene; water 3: 0.5 h / 20 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C24H24OS

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol 2.1: thionyl chloride / Inert atmosphere; Cooling with ice 2.2: Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -84 °C / Inert atmosphere 3.2: 1 h / 120 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C25H26OS

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol 2.1: thionyl chloride / Inert atmosphere; Cooling with ice 2.2: Inert atmosphere 3.1: 2 h / 20 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C16H16OS

Conditions	Yield
With methanol; sodium tetrahydroborate

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 9-(phenylthio)-2-isopropyl-9H-thioxanthene

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol 2: perchloric acid / toluene; water View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 9-(methylthio)-2-isopropyl-9H-thioxanthene

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; methanol 2.1: thionyl chloride / Inert atmosphere; Cooling with ice 2.2: Inert atmosphere View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C27H27O6S(1+)*CF3O3S(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C26H24O6S

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C 3.1: sodium hydroxide; water / chloroform / 1.5 h / 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C25H22O6S

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C 3.1: sodium hydroxide; water / chloroform / 1.5 h / 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C26H25O6S(1+)*CF3O3S(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C25H22O4S

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: trifluorormethanesulfonic acid / chloroform / 0.5 h / 23 °C 2.2: 6.25 h / 5 - 23 °C View Scheme

Upstream product

• 98-82-8 Isopropylbenzene 
• 5495-75-0 2-(4-isopropylphenylthio)benzoic acid 
• 3950-02-5 2-chlorosulfenylbenzoyl chloride 
• 119-80-2 2,2'-dithiobenzoic acid 
• 98-07-7 Benzotrichlorid 

Downstream Products

• 482662-60-2 2-isopropylthioxanthone sulphoxide 
• 210295-96-8 2-isopropyl-9H-thioxanthen-9-one 10,10-dioxide 
• 162881-26-7 phenyl bis(2,4,6-trimethylbenzoyl)phosphine oxide 
• 474510-57-1 2-hydroxy-1-(4-(4-(2-hydroxy-2-methylpropionyl)-benzyl)-phenyl)-2-methylpropan-1-one 

Relevant articles and documents

Preparation method of thioxanthone photoinitiator

The invention relates to a preparation method of a thioxanthone photoinitiator, particularly relates to a preparation method of 2,4-diethyl thioxanthone and isopropyl thioxanthone, and is characterized in that the 2,4-diethyl thioxanthone and isopropyl thioxanthone are prepared by taking dithiosalicylic acid as a raw material and adopting a combined catalyst, and the 2,4-diethyl thioxanthone and isopropyl thioxanthone are both thioxanthone photoinitiators. According to the method, the catalyst can be recycled and reused, and meanwhile, the defects that a large amount of sulfuric acid is used and a large amount of sulfonation byproducts are generated in the reaction in the traditional process are avoided. According to the method, the raw materials are cheap and easy to obtain, the yield is high, the catalyst can be recycled and continuously used, and the preparation method is cheap, environmentally friendly, easy to operate and suitable for industrialization.

Ultraviolet-light-induced aerobic oxidation of benzylic C(sp3)-H of alkylarenes under catalyst- and additive-free conditions

A mild and efficient system has been discovered for the synthesis of α-aryl carbonyl compounds via oxidation of benzylic C–H to C[dbnd]O bonds. This ultraviolet-light-mediated oxygenation reaction exhibited excellent substrate scope including various xanthenes, thioxanthenes and 9, 10-dihydroacridines and afforded the corresponding ketones with good to excellent yields under catalyst- and additive-free conditions at room temperature.

Preparation method of 2-isopropylthioxanthone

The invention relates to a preparation method of a photoinitiator 2-isopropylthioxanthone. The method is concretely characterized in that 2-(4-isopropylthiophenyl)benzoic acid undergoes a ring-closingreaction under a refluxing dehydration condition to prepare the 2-isopropylthioxanthone. The method has the advantages of small use amount of concentrated sulfuric acid, small environmental pressureand good product appearance.